GUIDE • 1040-ES SAFE HARBOR

The 110% Safe Harbor Rule, With Real Numbers

The most useful tax rule most freelancers have never read. One known number, four payments, and no underpayment penalty, no matter how good your year turns out.

GUIDE • 1040-ES DUE DATES

Quarterly Estimated Tax Due Dates for 2026 and 2027

The 2026 dates are April 15, June 15, and September 15, 2026, plus January 15, 2027. As of today, two of those have passed, so this is a calendar for what is left and a head start on planning 2027.

Estimated tax dates look like they should be simple, four evenly spaced deadlines, and they are not. The IRS splits the year into uneven chunks, one of the deadlines lands in January of the following year, and the whole schedule shifts whenever a date hits a weekend or holiday. I keep this calendar pinned because the one time I trusted my memory, I paid the January installment two weeks late and bought myself a penalty notice.

The remaining 2026 date

Income earnedPayment due
September 1 to December 31, 2026January 15, 2027 (Friday)

That is it for 2026. The April, June, and September 2026 payments are behind us. If you missed the September 15 payment, pay it now anyway: the underpayment penalty accrues from the due date until you pay, so every week you wait makes it worse. A catch-up payment does not erase the penalty for the missed quarter, but it stops it from growing.

The full 2027 schedule

Income earnedPayment due
January 1 to March 31, 2027April 15, 2027 (Thursday)
April 1 to May 31, 2027June 15, 2027 (Tuesday)
June 1 to August 31, 2027September 15, 2027 (Wednesday)
September 1 to December 31, 2027January 18, 2028 (Monday)

Two quirks worth noting. The 2027 dates are the statutory schedule with the weekend and holiday rule applied; the IRS had not released the 2027 Form 1040-ES at the time of writing, so confirm against it when it publishes. And the final 2027 payment slides to January 18, 2028, because January 15 is a Saturday and the following Monday is the Martin Luther King Jr. holiday. The IRS moves any deadline that lands on a weekend or DC legal holiday to the next business day.

Why the "quarters" are uneven

The payment periods are three months, two months, three months, and four months. The short second quarter, April and May only, is the one that trips people up: income earned in June belongs to the third quarter, not the second. If your income is lumpy, do not just divide your annual estimate by four. The annualized income installment method on Form 2210 lets you match payments to when the income actually arrived, which is the correct tool for seasonal earners.

Frequently asked questions

Are estimated taxes really due four times a year?

Yes, if you expect to owe $1,000 or more after withholding and credits and your withholding will not cover the safe harbor. The IRS runs on pay-as-you-go: employees pay through withholding, everyone else pays quarterly.

What if I started freelancing in the middle of the year?

You only owe estimated payments for the quarters in which you had the income. Use the annualized income installment method to show the IRS when the income arrived, so you are not penalized for quarters before you started earning.

Can I skip the quarterly payments and just pay everything in January?

Not without risk. The underpayment penalty is calculated per quarter, so a single January payment leaves the first three quarters short. The safe harbor rules are the way to avoid the penalty, not timing tricks.

Do states follow the same estimated tax dates?

Many states mirror the federal schedule, but not all, and state safe harbor rules differ. Check your state revenue department rather than assuming the federal dates apply.

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Related reading: The 110% Safe Harbor Rule, With Real Numbers · I Missed a Quarterly Estimated Tax Payment. Now What?